Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to San José from $205

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to San José

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:04 am - 12:00 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
6h 56m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:25 pm - 12:47 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
22h 22m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$383Delta
Wed, Oct 28 - Thu, Nov 5
Delta Logo
6:44 pm - 12:00 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
18h 16m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
Delta Logo
2:30 pm - 9:42 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
19h 12m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$383Delta
Tue, Oct 27 - Wed, Nov 11
Delta Logo
6:44 pm - 12:00 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
18h 16m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
Delta Logo
2:25 pm - 6:00 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
27h 35m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$383Delta
Tue, Oct 27 - Fri, Nov 6
Delta Logo
9:30 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
12h 45m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 10:56 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
15h 56m1 stop Atlanta Hartsfield-Jackson
$383Delta
Wed, Nov 11 - Tue, Nov 24
Delta Logo
6:44 pm - 12:00 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
18h 16m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
Delta Logo
2:30 pm - 10:56 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 26m1 stop Atlanta Hartsfield-Jackson
$383Delta
Tue, Oct 27 - Tue, Nov 10
Delta Logo
6:44 pm - 12:00 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
18h 16m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
Delta Logo
2:30 pm - 12:35 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
22h 05m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$383Delta
Tue, Oct 27 - Mon, Nov 9
Delta Logo
9:30 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
12h 45m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 9:42 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
26h 42m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$383Delta
Wed, Nov 11 - Tue, Nov 24
Delta Logo
6:44 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
27h 31m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 10:56 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
15h 56m1 stop Atlanta Hartsfield-Jackson
$383Delta
Sat, Nov 14 - Tue, Nov 24
Southwest Logo
5:25 am - 1:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 20m1 stop Houston Hobby
Southwest Logo
2:45 pm - 10:45 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 00m1 stop Houston Hobby
$434Southwest
Mon, Feb 1 - Mon, Feb 8
Southwest Logo
5:00 am - 12:35 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 35m1 stop Orlando
Southwest Logo
2:15 pm - 11:05 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 50m1 stop Houston Hobby
$434Southwest
Thu, Oct 29 - Tue, Nov 3

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Delta flights from Chicago Midway Airport to San José

Our best Delta deals on Chicago Midway Airport to San José flight tickets
Delta
Oct 27
MDW6:44 pmChicago Midway
18h 16m
2 stops
SJO12:00 pmSan José Juan Santamaria Intl
Nov 6
SJO2:25 pmSan José Juan Santamaria Intl
8h 08m
1 stop
MDW10:33 pmChicago Midway
$383
Delta
Nov 17
MDW1:00 pmChicago Midway
9h 15m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
Nov 24
SJO7:00 amSan José Juan Santamaria Intl
15h 56m
1 stop
MDW10:56 pmChicago Midway
$395
Delta
Oct 5
MDW7:01 pmChicago Midway
17h 59m
2 stops
SJO12:00 pmSan José Juan Santamaria Intl
Oct 21
SJO1:25 pmSan José Juan Santamaria Intl
18h 52m
2 stops
MDW9:17 amChicago Midway
$400

Southwest flights from Chicago Midway Airport to San José

Our best Southwest deals on Chicago Midway Airport to San José flight tickets
Southwest
Oct 29
MDW5:00 amChicago Midway
8h 35m
1 stop
SJO12:35 pmSan José Juan Santamaria Intl
Nov 3
SJO2:15 pmSan José Juan Santamaria Intl
8h 50m
1 stop
MDW11:05 pmChicago Midway
$434
Southwest
Nov 9
MDW8:40 pmChicago Midway
15h 40m
2 stops
SJO12:20 pmSan José Juan Santamaria Intl
Nov 13
SJO1:20 pmSan José Juan Santamaria Intl
9h 35m
1 stop
MDW10:55 pmChicago Midway
$438
Southwest
Oct 5
MDW11:50 amChicago Midway
8h 50m
1 stop
SJO7:40 pmSan José Juan Santamaria Intl
Oct 14
SJO9:00 amSan José Juan Santamaria Intl
8h 35m
1 stop
MDW6:35 pmChicago Midway
$452

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Wed 10/28

6:04 am-12:00 pm

1 stop6h 56m

San José Juan Santamaria Intl

Thu 11/5

2:25 pm-12:47 pm

2 stops22h 22m

$383

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Tue 10/27

6:44 pm-12:00 pm

2 stops18h 16m

San José Juan Santamaria Intl

Wed 11/11

2:30 pm-9:42 am

2 stops19h 12m

$383

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Tue 10/27

6:44 pm-12:00 pm

2 stops18h 16m

San José Juan Santamaria Intl

Fri 11/6

2:25 pm-6:00 pm

2 stops27h 35m

$383

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Wed 11/11

9:30 am-10:15 pm

2 stops12h 45m

San José Juan Santamaria Intl

Tue 11/24

7:00 am-10:56 pm

1 stop15h 56m

$383

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Tue 10/27

6:44 pm-12:00 pm

2 stops18h 16m

San José Juan Santamaria Intl

Tue 11/10

2:30 pm-10:56 pm

1 stop8h 26m

$383

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Tue 10/27

6:44 pm-12:00 pm

2 stops18h 16m

San José Juan Santamaria Intl

Mon 11/9

2:30 pm-12:35 pm

2 stops22h 05m

$383

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Wed 11/11

9:30 am-10:15 pm

2 stops12h 45m

San José Juan Santamaria Intl

Tue 11/24

7:00 am-9:42 am

2 stops26h 42m

$383

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Sat 11/14

6:44 pm-10:15 pm

2 stops27h 31m

San José Juan Santamaria Intl

Tue 11/24

7:00 am-10:56 pm

1 stop15h 56m

$383
Quickest round-trip

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Mon 2/1

5:25 am-1:45 pm

1 stop8h 20m

San José Juan Santamaria Intl

Mon 2/8

2:45 pm-10:45 pm

1 stop8h 00m

$434

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Thu 10/29

5:00 am-12:35 pm

1 stop8h 35m

San José Juan Santamaria Intl

Tue 11/3

2:15 pm-11:05 pm

1 stop8h 50m

$434

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to San José from

How to get the cheapest flight ticket from Chicago Midway Airport to San José

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to San José?

On average, the least expensive day to fly to San José from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $516. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago Midway Airport to San José on a Saturday will generally be more expensive and average around $723. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to San José?

Our data shows that the cheapest Chicago Midway Airport to San José flights are usually those with departure times in the afternoon. Our users have found flights to San José in the afternoon for as low as $514. Flights at noon are often more expensive with an average ticket price of $696.

When to book flights from Chicago Midway Airport to San José

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San José according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San José (MDW to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José

Best Price Found

$205

Fastest flight time

6h 45m

Direct flights

None
The best one-way flight to San José from Chicago Midway Airport in the past 72 hours is $205. The best round-trip flight deal from Chicago Midway Airport to San José found on momondo in the last 72 hours is $383.
The fastest flight from Chicago Midway Airport to San José takes 6h 45m
There are no direct flights from Chicago Midway Airport to San José. There are no popular flight routes from Chicago Midway Airport to San José.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to San José

  • How far is Chicago Midway to San José Juan Santamaria Intl by plane?

    A flight from Chicago Midway to San José Juan Santamaria Intl will travel around 2210.5 mi. Typically, this will take 6h 45m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    Prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents you'll need for your trip to San José Juan Santamaria Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to San José?

Best airlines flying from Chicago Midway Airport to San José

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $394Free CancellationRating
8.0
4,214 reviews
Search Southwest flights

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Monteverde
Alajuela
Heredia
Santa Elena
San Gerardo de Dota
Dominical
Esterillos Este

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José?

Finding the right flight to San José from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San José quick and easy, saving you time and money.

Can I find flights from Chicago to San José with flexible booking policies on momondo?

All flight searches from Chicago to San José on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San José?

momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San José flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your San José trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 9/22
Tue 9/29
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Costa Rica